Hi @sean_clayton1 ---- Thank you for the follow up and providing the requested screenshots, both are very appreciated! Apologies for the slow response.
Moving forward, may I kindly ask you for the following:
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A brief but accurate description of your current setup as seen here.
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A screenshot of your “storage” tab found under “settings”, in Roon.
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Can you please confirm that the iTunes playlist was built by you personally and not something that perhaps was generated by iTunes (i.e smart playlist etc).
-Eric